Home / Publications / Synthesis and antimitotic activity of novel 5-aminoisoxazoles bearing alkoxyaryl moieties

Synthesis and antimitotic activity of novel 5-aminoisoxazoles bearing alkoxyaryl moieties

Dmitry Alekseevich Vasilenko 1
Dmitry Alekseevich Vasilenko
, 
Elena Borisovna Averina 1, 2
Elena Borisovna Averina
, 
Nikolay Alekseevich Zefirov 1
Nikolay Alekseevich Zefirov
, 
Birgit Wobith 3
Birgit Wobith
,  , 
Viktor Borisovich Rybakov 1
Viktor Borisovich Rybakov
, 
Ol'ga Nikolaevna Zefirova 1, 2
Ol'ga Nikolaevna Zefirova
, 
Tamara Stepanovna Kuznetsova 1
Tamara Stepanovna Kuznetsova
, 
Sergei A Kuznetsov 3
Sergei A Kuznetsov
, 
Nikolai Serafimovich Zefirov 1, 2
Nikolai Serafimovich Zefirov
10.1016/j.mencom.2017.05.003
Published 2017-04-25
Communication , Volume 27, Issue 3, 228-230
23
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Vasilenko D. A. et al. Synthesis and antimitotic activity of novel 5-aminoisoxazoles bearing alkoxyaryl moieties // Mendeleev Communications. 2017. Vol. 27. No. 3. pp. 228-230.
GOST all authors (up to 50) Copy
Vasilenko D. A., Averina E. B., Zefirov N. A., Wobith B., Grishin Y. K., Rybakov V. B., Zefirova O. N., Kuznetsova T. S., Kuznetsov S. A., Zefirov N. S. Synthesis and antimitotic activity of novel 5-aminoisoxazoles bearing alkoxyaryl moieties // Mendeleev Communications. 2017. Vol. 27. No. 3. pp. 228-230.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2017.05.003
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.05.003
TI - Synthesis and antimitotic activity of novel 5-aminoisoxazoles bearing alkoxyaryl moieties
T2 - Mendeleev Communications
AU - Vasilenko, Dmitry Alekseevich
AU - Averina, Elena Borisovna
AU - Zefirov, Nikolay Alekseevich
AU - Wobith, Birgit
AU - Grishin, Yuri Konstantinovich
AU - Rybakov, Viktor Borisovich
AU - Zefirova, Ol'ga Nikolaevna
AU - Kuznetsova, Tamara Stepanovna
AU - Kuznetsov, Sergei A
AU - Zefirov, Nikolai Serafimovich
PY - 2017
DA - 2017/04/25
PB - Mendeleev Communications
SP - 228-230
IS - 3
VL - 27
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2017_Vasilenko,
author = {Dmitry Alekseevich Vasilenko and Elena Borisovna Averina and Nikolay Alekseevich Zefirov and Birgit Wobith and Yuri Konstantinovich Grishin and Viktor Borisovich Rybakov and Ol'ga Nikolaevna Zefirova and Tamara Stepanovna Kuznetsova and Sergei A Kuznetsov and Nikolai Serafimovich Zefirov},
title = {Synthesis and antimitotic activity of novel 5-aminoisoxazoles bearing alkoxyaryl moieties},
journal = {Mendeleev Communications},
year = {2017},
volume = {27},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.05.003},
number = {3},
pages = {228--230},
doi = {10.1016/j.mencom.2017.05.003}
}
MLA
Cite this
MLA Copy
Vasilenko, Dmitry Alekseevich, et al. “Synthesis and antimitotic activity of novel 5-aminoisoxazoles bearing alkoxyaryl moieties.” Mendeleev Communications, vol. 27, no. 3, Apr. 2017, pp. 228-230. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.05.003.

Abstract

5-Aminoisoxazoles containing trimethoxy- and methylenedioxyphenyl moieties were prepared by heterocyclization of electrophilic alkenes with tetranitromethane in the presence of triethylamine with subsequent reduction of resulting 5-nitroisoxazoles. The crystal structure of 3,4,5-trimethoxybenzyl 5-aminoisoxazole-3-carboxylate was determined by X-ray analysis. Two novel 5-aminoisoxazoles demonstrated moderate antimitotic activity to human lung carcinoma A549 cell line.

References

1.
Bioisosterism:  A Rational Approach in Drug Design
Patani G.A., LaVoie E.J.
Chemical Reviews, 1996
3.
Zlotin S.G., Churakov A.M., Luk’yanov O.A., Makhova N.N., Sukhorukov A.Y., Tartakovsky V.A.
Mendeleev Communications, 2015
4.
Unexpected Heterocyclization of Electrophilic Alkenes by Tetranitromethane in the Presence of Triethylamine. Synthesis of 3-Nitroisoxazoles
Volkova Y.A., Averina E.B., Grishin Y.K., Bruheim P., Kuznetsova T.S., Zefirov N.S.
Journal of Organic Chemistry, 2010
5.
Heterocyclization of electrophilic alkenes with tetranitromethane revisited: regiochemistry and the mechanism of nitroisoxazole formation
Averina E.B., Samoilichenko Y.V., Volkova Y.A., Grishin Y.K., Rybakov V.B., Kutateladze A.G., Elyashberg M.E., Kuznetsova T.S., Zefirov N.S.
Tetrahedron Letters, 2012
6.
Chemoselective Reduction of Functionalized 5-Nitroisoxazoles: Synthesis of 5-Amino- and 5-[Hydroxy(tetrahydrofuran-2-yl)amino]isoxazoles
Averina E., Vasilenko D., Samoilichenko Y., Grishin Y., Rybakov V., Kuznetsova T., Zefirov N.
Synthesis, 2014
7.
A Common Pharmacophore for a Diverse Set of Colchicine Site Inhibitors Using a Structure-Based Approach
Nguyen T.L., McGrath C., Hermone A.R., Burnett J.C., Zaharevitz D.W., Day B.W., Wipf P., Hamel E., Gussio R.
Journal of Medicinal Chemistry, 2005
8.
Ligands of the colchicine site of tubulin: A common pharmacophore and new structural classes
Zefirova O.N., Diikov A.G., Zyk N.V., Zefirov N.S.
Russian Chemical Bulletin, 2007
9.
10.1016/j.mencom.2017.05.003_bib0045
Wu-Wong
Cancer Res., 2001
11.
Synthesis and biological evaluation of novel 5-hydroxylaminoisoxazole derivatives as lipoxygenase inhibitors and metabolism enhancing agents
Averina E.B., Vasilenko D.A., Gracheva Y.A., Grishin Y.K., Radchenko E.V., Burmistrov V.V., Butov G.M., Neganova M.E., Serkova T.P., Redkozubova O.M., Shevtsova E.F., Milaeva E.R., Kuznetsova T.S., Zefirov N.S.
Bioorganic and Medicinal Chemistry, 2016
12.
Zinc Promoted Mild and Efficient Method for the Esterification of Acid Chlorides with Alcohols
Yadav J.S., SudershanReddy G., Srinivas D., Himabindu K.
Synthetic Communications, 1998
16.
Development of small-molecule probes that selectively kill cells induced to express mutant RAS.
Weïwer M., Bittker J.A., Lewis T.A., Shimada K., Yang W.S., MacPherson L., Dandapani S., Palmer M., Stockwell B.R., Schreiber S.L., Munoz B.
Bioorganic and Medicinal Chemistry Letters, 2012
17.
Unusual Tubulin-Clustering Ability of Specifically C7-Modified Colchicine Analogues
Zefirova O.N., Lemcke H., Lantow M., Nurieva E.V., Wobith B., Onishchenko G.E., Hoenen A., Griffiths G., Zefirov N.S., Kuznetsov S.A.
ChemBioChem, 2013
18.
Synthesis and biological testing of (5Z)-2-aryl-5-arylmethylidene-3,5-dihydro-4H-imidazol-4-ones as antimitotic agents
Beloglazkina A.A., Wobith B., Barskaia E.S., Zefirov N.A., Majouga A.G., Beloglazkina E.K., Zyk N.V., Kuznetsov S.A., Zefirova O.N.
Medicinal Chemistry Research, 2016
19.
Zefirova O.N., Nurieva E.V., Lemcke H., Ivanov A.A., Zyk N.V., Weiss D.G., Kuznetsov S.A., Zefirov N.S.
Mendeleev Communications, 2008